Tetrahydrofuran → HCID 20392276, compound

Participants

Reaction Steps

A reaction mixture comprising 5 g. of 4-acetyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 225 ml. of dried tetrahydrofuran and 6.4 g. of lithium aluminum hydride in 150 ml. of dried tetrahydrofuran under nitrogen is stirred with heating to reflux overnight. A 6.5 ml. portion of water is added cautiously with stirring and cooling followed by 6.5 ml. of 15% sodium hydroxide and 19 ml. of water. The complex is filtered and washed thoroughly with ether. The combined filtrate and washings is dried over sodium sulfate and concentrated to a dark brown viscous oil. The oil is crystallized by treatment with 50 ml. of ether:hexane (50:50). The crystalline product is dissolved in 15 ml. of 40% methylene chloride in hexane and chromatographed on an alumina column eluting with 40% methylene chloride in hexane. Fractions 2-8 (50 ml. each) are combined and concentrated giving olive green crystals. These crystals are triturated in hexane, washed with hexane and dried giving the desired product, mp. 85°-87° C.

Provenance & Evidence